Basic information
- CAS
5273-86-9- Standard SMILES
C/C=C\c1cc(OC)c(OC)cc1OC- InChIKey
RKFAZBXYICVSKP-WAYWQWQTSA-N- Molecular formula
- C12H16O3
- Average molar mass
- 208.25 g/mol
- Monoisotopic mass
- 208.10994437
Overview
Asarone is a phenylpropanoid that is benzene substituted by methoxy groups at positions 1, 2 and 4 and a propen-1-yl group at position 5. It has been isolated from Acorus. It has a role as a plant metabolite. It is an alkenylbenzene, a phenylpropanoid and a member of methoxybenzenes.
Names & identifiers
- Preferred name
- Beta-Asarone
- IUPAC
- 1,2,4-trimethoxy-5-[(Z)-prop-1-enyl]benzene
- English name
- BETA-ASARONE
- Molecular formula
- C12H16O3
- Molecular weight
- 208.25
Names & synonyms
beta-Asarone5273-86-9(Z)-Asaronecis-Isoelemicincis-Asaronecis-IsoasaroneIGA3MH6IUW1,2,4-trimethoxy-5-[(Z)-prop-1-enyl]benzene(Z)-5-Propenyl-1,2,4-trimethoxybenzenecis-beta-Asarone2,4,5-Trimethoxypropen-1-ylbenzene(Z)-1,2,4-Trimethoxy-5-(1-propenyl)benzene
Show more names
β-AsaroneB-ASARONEC10430ASARONE, B-β-Asarone-RMCis-β-asarone
Benzene, 1,2,4-trimethoxy-5-(1-propenyl)-, (Z)-BENZENE, 1,2,4-TRIMETHOXY-5-PROPENYL-, (Z)-1,2,4-trimethoxy-5-propenylbenzene, z-CHEBI:10353DTXCID00911420DTXSID6010200571,2,4-trimethoxy-5-((Z)-prop-1-enyl)benzeneRefChem:29765
Database identifiers
- CAS
5273-86-9- PubChem CID
- 5281758
- DTXSID
DTXSID601020057- ChEMBL
CHEMBL477752- ChEBI
CHEBI:78308
Properties
Computed structural properties
- XLogP
- 3
- Topological polar surface area
- 27.7 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 4
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 203
Experimental & physicochemical properties
FragrancesFragrance substance (cis-and trans-Asarone) -> IFRA amendment 40
Physicochemical properties
- Boiling point
- 296 ℃ · 296℃
- Density
- 1.073 g/mL · 1.073 g/mL at 25 °C(lit.)
- refractive index
- 20 · n20/D 1.558(lit.)
- Flash point
- 230 °F · >230 °F
- storage temp.
- -20 °C · -20°C
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
- Solid
- color
- Colourless to Pale Yellow
- BRN
- 1910605 · 1910605
- Stability
- Light Sensitive
- InChI
- 1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3/b6-5-
- InChIKey
- RKFAZBXYICVSKP-WAYWQWQTSA-N
- SMILES
- [H]\C(C)=C(/[H])c1cc(OC)c(OC)cc1OC
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P273, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 168 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- rtecs
- DC3000000
- hs_code
- 29093090
- Toxicity
- cyt-hmn-lym 107 mg/L PLMEAA 53,251,87
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 23-24/25
- Storage Class
- 10 - Combustible liquids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P301+P312+P330
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included.
Fibrinolysin or agents that convert plasminogen to FIBRINOLYSIN.
Uses & manufacturing
IFRA Fragrance Standards
cis-and trans-Asarone
494-40-6:; Benzene, 1,2,4-trimethoxy-5-(1-propen-1-yl)- (unspecified isomer); (E)-and (Z)-2,4,5-Trimethoxypropen-1-yl benzene); 2883-98-9:; α-Asarone; trans-Asarone; Benzene, 1,2,4-trimethoxy-5-(1-propenyl)-, (E)-; trans-Isoasarone; 5273-86-9:; Ã-Asarone; cis-Ã-Asarone; Benzene, 1,2,4-trimethoxy-5-(1-propenyl)-, (Z)-; cis-Isoasarone
IFRA_STD_110.pdf
40
IFRA 51st Amendment - Guidance for the use of IFRA Standards
Prohibition: This material should not be used as a fragrance ingredient_Restriction: This material should be used only in the limited quantity as stated in the Standard
Use ClassificationFlavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Applications
UsesGrain fumigant, insect chemisterilant.
Usescis-2,4,5-Trimethoxy-1-propenylbenzene (β-Asarone) was used in preparation of:2,4,5-trimethoxycinnamaldehyde and 2,4,5-trimethoxycinnamyltosylhydrazone1-(2,4,5-trimethoxyphenyl)-1,2-dihydroxypropane
UsesReference standard in the analysis of herbal medicinal products.
General Descriptioncis-2,4,5-Trimethoxy-1-propenylbenzene is an antibiotic and was isolated from the extract of Acorus gramineus using various chromatographic procedures.
Related reactions
5 records
Compound notes
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